| Identification | More | [Name]
2-Amino-6-nitrobenzothiazole | [CAS]
6285-57-0 | [Synonyms]
2-AMINO-6-NITROBENZOTHIAZOLE
6-NITRO-1,3-BENZOTHIAZOL-2-AMINE
6-NITRO-2-AMINOBENZOTHIAZOLE
6-NITRO-2-BENZOTHIAZOLAMINE
6-NITRO-BENZOTHIAZOL-2-YLAMINE
IFLAB-BB F1386-0392
LABOTEST-BB LT00454107
6-nitro-2-benzothiazolamin
6-nitro-1,3-benzothiazol-2-ylamine
6-nitrobenzothiazol-2-amine
6-Nitrobenzo[d]thiazol-2-amine
2-AMINO-6-NITROBENZOTHIAZOLE, 97+%
2-Amino-6-NitroBenzothiazole(Nabtho)
2-Benzothiazolamine,6-nitro-(9CI)
2-Amino-6-nitrobenzothiazol | [EINECS(EC#)]
228-513-7 | [Molecular Formula]
C7H5N3O2S | [MDL Number]
MFCD00005786 | [Molecular Weight]
195.2 | [MOL File]
6285-57-0.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow crystalline powder | [Melting point ]
247-249 °C (lit.) | [Boiling point ]
411.7±37.0 °C(Predicted) | [density ]
1.4666 (rough estimate) | [refractive index ]
1.6740 (estimate) | [storage temp. ]
2-8°C, protect from light | [pka]
1.76±0.10(Predicted) | [InChI]
1S/C7H5N3O2S/c8-7-9-5-2-1-4(10(11)12)3-6(5)13-7/h1-3H,(H2,8,9) | [InChIKey]
GPNAVOJCQIEKQF-UHFFFAOYSA-N | [SMILES]
Nc1nc2ccc(cc2s1)[N+]([O-])=O | [CAS DataBase Reference]
6285-57-0(CAS DataBase Reference) | [EPA Substance Registry System]
6285-57-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
2
| [RTECS ]
DL0865000
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29342000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [General Description]
Orange crystals or yellow powder. | [Reactivity Profile]
2-AMINO-6-NITROBENZOTHIAZOLE(6285-57-0) is incompatible with strong oxidizing agents and strong acids. | [Air & Water Reactions]
Insoluble in water. | [Fire Hazard]
Flash point data for this compound are not available; however, 2-AMINO-6-NITROBENZOTHIAZOLE is probably combustible. | [Chemical Properties]
yellow crystalline powder | [Uses]
2-Amino-6-nitrobenzothiazole has been used:
- as model analyte for voltammetric determination of electrochemically reducible organic substances
- in the synthesis of 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid[2-(cyclohexanecarbonylamino)benzothiazol-6-yl]amide derivatives
- in the preparation of push-pull nonlinear optical chromophores containing thiazole and benzothiazole acceptors
- as a base in dye production by diazotation reaction
| [Synthesis]
GENERAL METHOD: A solution of 4-nitroaniline (2 mmol) in acetonitrile (15 ml) was slowly added to a solution of potassium thiocyanate (8 mmol) in acetonitrile (15 ml). Subsequently, 0.06 g (30 mol%) of BF3/SiO2 nanocatalyst was added to the reaction system and the mixture was placed in an ice salt bath and mechanically stirred for 30 min. A solution of bromine (4 mmol, 0.2 ml) in acetonitrile (3 ml) was slowly added through a dropping funnel, and the dropping rate was controlled to ensure that the reaction temperature did not exceed 0 °C. After the addition of the bromine solution, the reaction continued to be stirred at room temperature for 4 h, during which the progress of the reaction was monitored by TLC. Upon completion of the reaction, the reaction mixture was poured into water, heated in a 70 °C water bath and thermally filtered to remove the catalyst. The catalyst was washed with acetone and recycled for reuse. The filtrate was neutralized to neutrality with 10% NaOH solution and the precipitated solid was collected by filtration, dried and recrystallized with ethanol (10 ml) to give the target product 2-amino-6-nitrobenzothiazole. The structure of the product was confirmed by the following physical and spectral data and verified by comparison with standards.
Spectral data of 2-amino-6-nitrobenzothiazole: yellow solid; yield = 93%; melting point = 202-204 °C (literature value 203 °C); FT-IR (KBr, cm^-1): 3315, 3012, 2835, 1580, 1476, 1261, 920, 742, 512; ^1H NMR (400 MHz, CDCl3 , δ ppm): 5.44 (s, 2H, NH2), 7.4-7.5 (d, 2H, Ar-H), 7.71 (s, 1H, Ar-H); ^13C NMR (100 MHz, DMSO-d6, δ ppm): 119, 120.9, 125.15, 126.07, 133.1, 152.15, 167.75. | [References]
[1] Synlett, 2012, vol. 23, # 15, p. 2219 - 2222
[2] Research on Chemical Intermediates, 2016, vol. 42, # 12, p. 7855 - 7868
[3] European Journal of Medicinal Chemistry, 2008, vol. 43, # 5, p. 1114 - 1122
[4] European Journal of Medicinal Chemistry, 2012, vol. 53, p. 41 - 51
[5] Russian Journal of Applied Chemistry, 2015, vol. 88, # 12, p. 2065 - 2073 |
|
|